I want to change careers, but how can I tell if I’m doing the right thing? Shall I wait a little longer? Is it better to stay in a job I hate while I line something else up or should I take a leap of faith and just quit?

If you’re in a job or career that’s not just a bad fit but is actually destroying your spirit, these questions probably run through your mind on a daily basis. And it’s a problem that’s worsened by friends and family who give polarising advice like, ‘Don’t worry, no one really likes their job” or “Just quit, life’s too short to not follow your passion”.

The fact is that while physically changing careers is easy, doing so and achieving the outcome you truly want is an art. So to help you do the latter, we’ve waded through a lot of books on this topic to bring you the best advice we’ve found on the subject.

Not sure if it’s the best time to change careers? Ask yourself the following questions.

What exactly is the problem and is a career change the best way to fix it?

“Most situations are simple – many are just emotionally difficult to act upon. The problem and solution are usually obvious and simple. It’s not that you don’t know what to do. Of course you do. You are just terrified that you might end up worse off than you are now.” Timothy Ferriss, The 4-Hour Work Week

Clarity is key to making a career change that will bring you whatever you’re looking for (be that happiness, fulfilment or more money) rather than just get you away from an intolerable work situation. And as Timothy Ferriss correctly points out in his best-selling book The 4-Hour Work Week, we all know what we want, but fear can stop us from admitting it to ourselves.

So, before making any decision about your career, it’s important for you to dig around your head a little and get clear about your end goal. Is it to get away from a job that’s making you miserable? If so, what about the job is causing misery? Is it the company you’re at? Your boss? Colleagues? Will your experience definitely be the same if you were to do the same job at a different company? Have you tried doing so?

A change of career is usually an ideal solution if you’re being pulled to do something else rather than if you’re just keen to run from a particularly bad job. If you’re really struggling to work out your true motivation for considering a career change, take a look at this cheat sheet. It will help you decide if the problem is your current job or career.

Do you know what career you want to change to and what that change will involve?

“Even if it doesn’t lead to a bulging bank account, it also shouldn’t lead to the poor house. Money isn’t everything, but it’s hard to love your life if you’re constantly stressed about paying the bills on time.” Chris Guillebeau, Born for This: How to Find the Work You Were Meant to Do

One of our favourite sayings is, “If you don’t know what to do, stand still” and it’s our favourite for a reason. If you want to make a career change but have no idea what you want to change to, how to get started and how you’ll financially support yourself through the change, it’s wise to put things on hold until you can answer these questions.

And while it pains us to bring up the issue of money, sadly, it’s something you need to seriously think about before leaving one job to pursue a brand new career. It’s easy to believe that as long as you’re doing something you love, money doesn’t matter, but as Chris Guillebeau points out in his book Born for This, unless you’re sitting on a huge trust fund, have lottery winnings in the bank or live on a desert island, you’ll need to be able to support yourself through your career transition and beyond… if you’re to avoid making the already stressful act of changing careers even more stressful.

Career experts always advise that you should have three to six months worth of pay saved up before quitting a job without having another one lined up. This is also true if you plan to start your new career by studying, interning or doing any other type of experience-gaining placement that doesn’t pay a salary you can exclusively live on.

right time to change careers
Make sure you understand exactly what your dream career involves before you make the change

Is your new career idea truly a good fit for you and your needs?

“Have you ever looked at what your idea of passion is? Most people haven’t. They’re trying to build a passionate life, all the while having no idea what it is. How can you know you’ve arrived if you don’t know what you’re after?” Henri Junttila, Find Your Passion: 25 Questions You Must Ask Yourself.

It can be pretty expensive, time-consuming and emotionally challenging to change careers, so if your true goal is to find work that’s truly aligned with you your passion, purpose or reason for being it pays to hold off on making the change until you’re confident that the career you want to switch to has the potential to give you what you’re looking for. We referenced Henri Junttila’s book Find Your Passion for this section because that’s where you need to start. Before saying a definite “yes” to a new career, you need to explore if it’s a good fit.

What are your strengths, weaknesses, skills, values, likes and dislikes? Does the field you’ve got your eye on look like one you can thrive in or are you about to jump from the frying pan to the fire?

This is one question that needs lots of research to be answered. Trust your gut to direct you to fields that may be a good fit, but do your research to make sure you’re going into something that will satisfy your needs. Many jobs look amazing on the outside but are completely different when you’re in them.

Rather than crossing your fingers and hoping for the best, find five people in the career field you’d like to move to and speak candidly with them. Find out what they do on a daily basis, what are the highs and lows of the job, what type of personalities do well in that field and most importantly, would they do their job if they won the lottery why or why not?

Are you mentally ready to go on a challenging journey that will be filled with tears, doubt and fear?

“When you do venture into new territory, be sure to create a back-up plan that will catch you if you falter. For example, ask someone you trust to be ‘on call’ to provide you with emotional or practical support in case you need it.” Ann Elizabeth Grace, Confusion to Clarity: The Twentysomething’s Guide to Finding Your Calling.

All too often, starting afresh is romanticised. Those who have found success are usually put forward as evidence of how great things will also be for you if you do the same. However, what they often fail to mention or gloss over is the fact that the journey can be very depressing. When you choose to leave a job that may suck but pays well and is stable, you’ll initially feel elated. But when the hustle to break into the field begins, you will very likely question yourself daily, blame yourself for being so stupid when things aren’t working out, feel belittled by those who don’t understand your decisions and continuously question them… oh and prepare to feel very alone.

However, there’s always a very bright light at the end of the tunnel, along with possibly everything you’ve ever wanted from a job. But to get there, you have to be mentally strong enough to persevere and keep going throughout the crappy times.

As Ann Elizabeth Grace says in Confusion to Clarity, there are no guarantees when you embark on a journey of change. In fact, the only certainty is that it won’t always be plain-sailing. This means you need to be at a place in life where you’re emotionally able to deal with this kind of challenge and/or have a great support system at hand. If other parts of your life are really stressful at present, it’s worth asking yourself if now is the best time for a career change. Remember that career changes don’t have to be all or nothing. If you can’t deal with the stress right now, but know a career change is something you need to do, there are less stressful and more gradual ways of making that change (e.g. trying your new career part-time, while staying in your current job).

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